$169

Located in the Berkshire mountains on more than 5 acres
surrounded by 29 acres of conservation land. Featuring
beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores, resturaunts, theaters, and events…

Enjoyable stay

Left on Aug 23, 2013 for a stay in August 2013

My husband and I stayed 2 nights at Riversong suite - a lower level studio/suite in Barbara and Philip's house. Their property is beautiful overlooking an open field and we enjoyed sitting in the rocking chairs in the gazebo out back. We enjoyed being away from congestion in a peaceful setting. Barbara has thought of everything in terms of furnishing and decorating the space and making sure …

$199

The Cottage, in picturesque Stockbridge, has the PERFECT location -- minutes from Main Street Lenox, Main Street Stockbridge, The Norman Rockwell Museum, Berkshire Botanical Gardens, Tanglewood Music Festival, The Shrine of the Divine Mercy at the Congregation of Marians, shops, theaters, hiking an biking.
Private…

Location, location, location

Left on Apr 09, 2011 for a stay in August 2006

This place is in one of the absolutely ideal locations in Berkshire Co. You are a 10 minute drive to Tanglewood (and away from all the traffic jams in Lenox and Lee) a walk to Stockbridge center, and Great Barrington is just down Route 7 a few miles. People who want to go to the theatre in Stockbridge or concerts at Tanglewood are nuts not to stay here. If you are not into a breakfast with 5 …

$250

Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16" floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains.
Country kitchen with dish washer, microwave, toaster …

Fantastic place to stay in the Berkshires

Left on Jan 08, 2014 for a stay in December 2013

Elaine was a very gracious host, and the...accommodations were lovely
and in a great location. The historic house has a lot of charm and many
nice updates, especially the clean, updated bathrooms and the huge
screened-in porch. ... We had room to spare, and everyone had a room to
themselves. The kitchen was well stocked, and the living room very cozy...
This would be a great place for skiers. …

$350

Enjoy all the Berkshires has to offer in our new (2014) restoration and outstanding renovation of the historic South Lee Schoolhouse. Perched on a hillside just across the road from the Housatonic River and Beartown State Forest in the hamlet of South Lee, just outside of Stockbridge, the 1892 schoolhouse has been …

$300

** Rental is only available for 2 week minimum during the summer (July - August)
Special Summer Deal -- Rent for the Season (July and August) and get either the last week in June OR the first week in September for half price!
This adorable cottage has all the ingredients for the ultimate retreat for body, mind and …

Great getaway!

Left on Feb 12, 2012 for a stay in August 2011

We had the most amazing time. This adorable home is so close to everything and yet is feels very private and secluded. It provided a perfect balance for relaxation and adventure. One of the best parts for us was the awesome lake. We certainly hope to come back very soon!

$150

Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts.
Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore quirky little shops …

Quaint & Cozy Condo!

Left on Jan 10, 2012 for a stay in December 2011

Having stayed at Gartner House a few times, I would recommend it to anyone looking for a comfortable getaway. It is a convenient, short walk to the center of Lenox allowing easy access to all of the wonderful little shops and some great places to eat.
The condo offers all the comforts of home including full kitchen, land line phone, microwave, washer/dryer and a small side yard. Its spacious …

Great getaway place, awesome host

Left on Jul 13, 2015 for a stay in July 2015

We stayed for a week over the 4th of July with our 3 kids, their spouses and our two little grandkids. The place was tough to find as GPS coordinates were off by 1/2 to 1 1/2 miles, but it was great to be away from everybody and everything in such a very nice house. The lake was full of water lilies from the dock to 1/3 across, but is pristine and secluded and we had a blast paddling in our …

$275

This is a beautiful Berkshire, post and beam private house nestled in the woods just off the Appalachian trail. Set on one of the Berkshires most coveted roads close to fresh water swimming in Lake Garfield, boating, fishing, classical outdoor concerts at Tanglewood & Skiing are all close by.
The Space
The large …

Awesome Venue!

Left on Jul 17, 2012 for a stay in June 2012

The Hill Cottage is absolutely charming. It is nestled in the forest surrounded by soaring, magnificent pines on a private country road. The atmosphere is very tranquil and peaceful. The cottage is spacious, clean, and well stocked.It is very comfortable and inviting. The cottage is rustic with attractive wide pine floors and knotty pine walls, yet it has very modern amenities including a Jacuzzi…

$499

We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen.
The house is newly constructed with ash hardwood floors, custom white pine trim and mahogany …

A true gem. New and beautiful with incredible space and wonderdul amenities, right in the heart of

Left on Jul 18, 2014 for a stay in July 2014

Our family of 5 rented this home over July 4th weekend and we couldn't have been more pleased. The home has just been newly renovated, is very tastefully appointed and looks and feels brand new both inside and out. It also has every amenity we could've hoped for, such as state-of-the-art kitchen appliances, wi-fi, cable TV plus Netflix, dual zone central air, a nice gas grill, multiple outdoor…

$225

Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the "Silo Studio", there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest from large screened…

$500

Located on the Santarella Estate, an historic site located in the the Massachussetts' Berkshires. The colonial home is the former residence of sculptor Sir Henry Hudson Kitson. The estate includes the landmark, iconic storybook style 'Gingerbread House,' designed by Kitson to look like an English Country Cottage, the …

$150

One bedroom air conditioned apartment with private entrance in 18th century house in Historic District of Stockbridge. Wonderful views of the river, 18th green of Stockbridge Golf Club and the Berkshire Hills. 5 minutes walk to the famous Red Lion Inn/town center.
Self contained and private. You have private bedroom …

Very nice and well kept place to stay, and owners were very gracious.

Left on May 29, 2015 for a stay in May 2015

Stayed 3 nights in the one-bedroom apartment connected to the main house. The apartment was very private, well kept and well appointed. Very quiet also. Owners were very accommodating and provided all that was needed for a pleasant trouble-free stay. The apartment was located a short 5-minute walk from downtown Stockbridge shops and restaurants.

$225

This 1600 sq. ft. cottage boasts everything you would need for your visit to the Berkshires whether it be for a full summer / winter season to explore this beautiful area or a quick getaway to Tanglewood,
The recently added master suite features a queen size bed, en-suite bathroom and a bonus separate sitting area…

$360

Beautiful house surrounded by protected woodland and a small beaver pond behind your backyard. All kinds of birds and wildlife. 5 Bedrooms, 2.5 baths, brand new kitchen, open living/dining room, laundry room. Wood stove that can function as a fireplace. 3 heating zones for comfort. All new electric and plumbing in …

Great Girlfriends' Getaway!

Left on Jan 31, 2012 for a stay in January 2012

We decided on fairly short notice to get away with a group of girlfriends to the Berkshires. Robin was so gracious to accommodate us on short notice. We arrived on a frigid day to find a clean and comfortable house, with a fire laid and ready for us. The kitchen had everything we needed for preparing our meals. We especially love the oversized coffee mugs! It's the little things that make a …

$125

The Smith Homestead in Alford Massachusetts has been homesteaded and farmed by our family for the past two centuries. Located on one of the nicest settings in the Berkshires, with 30 acres of fields and woods, and the crystal clear Alford Brook running through, we are central to all the cultural events and outdoor …

Beautiful

Left on Apr 09, 2013 for a stay in March 2013

Five stars! Perfect location for a getaway. A quick ride into the beautiful downtown Great Barrington. I have had many good night rests in this room. The hillside view is spectacular. And the best cup of coffee around.

$225

Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family.
The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd bedroom. A sofa in the …

Hidden Gem

Left on Jul 18, 2013 for a stay in July 2013

I would like to tell you not to go here. I would like to say stay away, that way it will be availible whenever we want to go back. It is the perfect place to use as a centre to see the area, or sit and do nothing. It was my wife, kids and grand mothers. We did hike, we did spend a day on the beach right by the house, but we also felt at ease to just sit on the screened porch and play cards or …

$375

Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands, wildlife and forest. It…

Big house, private, but a few drawbacks

Left on Sep 11, 2014 for a stay in August 2014

This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window. The playroom is a nice touch for those with kids. There are two staircases, which is also nice.

I was under the impression that there were four full bathrooms (which I took to mean with showers). When we arrived, we…

Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington)
The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows.. Nature lovers, artists…

Peaceful and relaxing weekend

Left on Sep 06, 2011 for a stay in August 2011

My husband and I stayed here while visiting Great Barrington for the weekend. The space is immaculate and very quaintly designed. There is ample space to spread out. Bed is comfortable, full bath is very clean and towels are provided. No stovetop, but a full fridge and kitchen sink. Not much need for a kitchen since downtown is just minutes away and offers plenty of excellent restaurants. The …

$150

first floor queensized bed, bath with shower. floors are wood ceiling has exposed beams and is furnished with oak antiques and a big wingbacked chair.built in bookshelf was from a companionway on a wooden sailing vessel owned by a sea captain that owned and ran the lodge back at the turn of the 20th century.
the …

I have stayed here several times

Left on Jun 17, 2014 for a stay in June 2013

And I hope to stay here again in the future. I feel very comfortable here - good privacy, the house is huge, rustic charm, generally very quiet. The property is massive - and the region is one of the most beautiful in the world.

Cozy and modern two bedroom and one bath vacation home with lake nearby
Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living room, fall foliage and…

Great home, great location

Left on Nov 26, 2013 for a stay in November 2013

Beautiful, modern and cosy home which proved to be a great base for the trip! The fire was an added treat at the end of the day! Location wise the cottage was perfect - close to some wonderful hikes, gorgeous villages and towns and some wonderful food options and restaurants. Already looking forward to the next visit!

$200

The Writer's Room is at the top of the stairs on the right. This handsome room is made completely of wood. Ceilings are higher and there's a sitting area in the big dormer. dormer faces east and get the morning sun!
The floors are wide plank cherry milled from the property. the walls are pine. there's a double bed, a…

vintage New England...home and hearth, the nearby arts and surrounding countryside

Left on Jun 17, 2014 for a stay in June 2013

We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is rustic 18th century all the way.

We either make our own meals or join in with others...cooking indoors and eating at the big banquet table, or outside at the BBQ.

$250

Welcome to our family getaway in the Berkshires which we also rent out. Set on 2 acres in the Stockbridge hamlet of Glendale, the house is conveniently located - just a short walk to the Norman Rockwell Museum, Chesterwood House, and Botanical Gardens. The sunny 1st floor features a living room with fireplace open to…

Great location, tired house

Left on Jul 30, 2014 for a stay in July 2014

Nice house but tired bathrooms and kitchen. One great bedroom, two so so. Hot one nite and needed non existing a/c. Great screened porch with view of water. Canoe was a plus. With a little updating and a good cleaning,it could be fantastic.

$650

This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the "illision of seclusion," as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater, shops, and more.
…

$200

Welcome to our School House Cottage located in the heart of the Berkshires. Set in front of the ledges of Warner Mountain, this historic home was originally a three room schoolhouse. An addition in the 1960's transformed it into a private home which it remained for many years. Now updated, the cottage has become a …

The perfect house for friends and family to share! Bright,uncluttered, and inviting, with privacy and views just minutes to town.
There are two fireplaces,a sunken living room, dining room with seating for 10, 4 bedrooms, 2 full bathrooms, and a cozy hang out area in the basement.
There is a washer and dryer, …

Best Memorable Thanksgiving Ever

Left on Feb 05, 2015 for a stay in November 2014

This was the first time we had a rental cottage, but it surpassed all of our expectations. The cottage was clean and well arranged. Kitchen was spacious enough for more than a few people cook together. Fireplace was lovely and so fun! The neighborhood was so quiet and calm. It snowed right before Thanksgiving, and the view was priceless! We would like to come back again!

$150

House is very private and located on 4 acres of Land. Back yard is peaceful and overlooks ponds. The backyard has a patio/picnic area with gas grill and firepit. One of the ponds has a spurting and lighted fountain that is relaxing ...so have a campfire at night and watch the lighted fountain for a relaxing evening. …

Quaint home on its own lake--don't miss this!

Left on Nov 29, 2014 for a stay in November 2014

The photos speak for themselves. Overall, the home was a great escape from city life, and included its own scenery and lake. My only complaint is that our stay was so short-lived. From our email communication with the owners, they seemed just as charming. We'll be back again.

$135

Fantastic spot for families and for those looking for a quiet getaway. Come have some summer fun, enjoy the autumn colors or play in the snow. This year round cottage is the perfect spot for those who enjoy outdoor activities.
The house is on a private dead end road, has a wonderful lake view and very private …

Best little hidden treasure

Left on Jul 07, 2010 for a stay in June 2010

We contacted the owners on a referal from a friend and had all our questions answered and more in regards to the propery and its amenities . Upon our arrival we got out of the car and was immediately greeted with a spectacular view of the lake. The house , was immaculate , clean , organized and big enough for me and my family to feel at home. We had a fantastic vacation and I would highly …

$300

This house is a perfect family retreat in the Berkshires. Nestled in the Village of Housatonic you will be centrally located to all Berkshire attractions. Less that ten minutes from skiing and Tanglewood, as well as the shops and restaurants of Stockbridge, Lenox, and Great Barrington, this is really the ideal …

Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private Visit our web-site ataberkshirehomeThe Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is a destination, a …

A memorable weekend getaway includes the most perfect house..

Left on Apr 17, 2013 for a stay in July 2012

My husband and I had the pleasure to rent out this house last summer with another married couple and their son. Although our daughter and their son truly enjoyed Tanglewood and our visits into Town (which are both extremely close), I can't help but think that my favorite part of our vacation was the house we were staying in! The space felt both warm and welcoming and fit our group size perfectly…

$643

This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 7,000 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses). It is on 9 …

$139

Pretty cottage in the woods on a beautiful private lake with a stream running through the property's two acres of land. Newly constructed, spacious and sunny second floor with views of the lake. Hardwood floors throughout the house. Swim, kayak, canoe or fish from the back yard, or just lounge all day watching the …

Idyllic retreat

Left on Oct 08, 2012 for a stay in October 2012

Quiet rural getaway in a beautiful setting. The backyard ends in the pond shown in the picture, which is surrounded by trees in full fall color. I spent a few hours perched at its edge and lost track of time for the first time in weeks. A complete absence of traffic noise means that the only outside sounds are of running water and rustling leaves, so you can hear yourself breathe. Not much by way…

$109

Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring new towns and attractions, or just spending a lazy afternoon reading on the screened-in porch? Get back to those simple pleasures in our cabin, which is located in a beautiful, quiet country …

Quaint,relaxing Berkshire getaway

Left on May 20, 2013 for a stay in April 2013

We really enjoyed our stay at your cottage---it was just what we were hoping for! You do a wonderful job of making sure everything's covered with the detailed instruction list, and all the amenities you advertise are just as you said. We loved being able to take the canoe out on the lake, and we used the firepit the first evening we arrived. The cottage itself is great,and we felt right at home…

$350

Attractive year-round lakefront house in a wooded area on a pristine Round Pond in the Berkshires. Relax and enjoy the view from your deck or dock. Fish from the dock or take the boat out onto the lake. Ideal family retreat in Great Barrington and only a short drive to cultural attractions (Tanglewood, Rockwell Museum…

$100

A Fully-Furnished Extended Stay property in the Berkshires. Located across the street from the Colonial Theatre and within minutes of most Berkshire County attractions.
Each spacious, efficiency (condo-style) single bedroom apartment includes living room, kitchen with full size appliances, bathroom, and deck.
Enjoy …

Excellent Rooms Plus Exceptional Service

Left on Jul 03, 2013 for a stay in January 2013

WOW, this place was very nice! What you get is a place with a five minute walk from downtown, well kept buidlings and grounds, excellent floor plans, new furniture, modern kitchen, large closets, a lot of storage space, outside deck, deckbawasher and dryer in the basement, latest technology i.e. cable TV, internet, maid service twice a week.

$250

Experience a little of old New England. Our vacation rental is a charming historic family farmhouse apartment with lots of room and comfort,2100Sq.ft., situated on 22 acres. Built in 1782, our farm was famous for breeding Plymouth Barred Rock chickens. In the 1800's, one of these barred rock roosters won the grand …

$130

Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large kitchen with all new …

$122

Lovely house on pond, Beautiful views of pond from every room, except one. Lounge on the deck with a glass of wine watch the Great Blue Heron has he stalks his fish, see the beavers swim lazily across the pond, flapping their tails to let you know they are there. Every room but one has a water view. Bedroom sleeps …

$375

Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests. 88 acres of land with views of Mt. Washington and Mount Everett promises privacy, …

home on the range

Left on Jul 08, 2010 for a stay in May 2003

my wife and i stayed at this lovely home for the entire summer, may through october, and we returned during the new year holiday the following winter. the setting is extremely private and sits on a gorgeous field surrounded on one side by the mountains and the other side of woods and cleared fields with an infinite skyscape, especially interesting on a starry night for heaven seekers.
the home …

$250

Surrounded by one of the most beautiful gardens in the Berkshires, Maya's Garden House is an outstanding example of an 18th century barn converted into a modern, comfortable, semi-secluded home. Located less than a mile from Great Barrington, it is close to everything the Berkshires are famous for; Tanglewood, Jacob's…

$250

In 1832, Josiah Loomis bought a parcel of land "and the structures thereon", along what was then known as "Massachusetts Turnpike No. 10," the toll road between Albany, NY and Hartford, CT.
Josiah Loomis, when he owned this property, could never have imagined what it would look like 180 years later. His 3 room …

$300

Charming 3 bedroom home nestled on 5 acres of secluded woods in the beautiful Berkshire Mountains. Located in the lovely town of Becket on a private road.
Completely updated home with a large, open floor plan. Master bedroom with attached private full bathroom on first floor, two additional bedrooms on second …

Comfortable and funky home for family vacation

Left on Jul 08, 2015 for a stay in July 2015

Lovely farmhouse, convenient to Tanglewood and shops in Lenox as well as other nearby towns and sights. We were a family of 7, including a 2 year old, and the swing set in the backyard was a great plus. Very comfortable furnishings with room for all. Enjoyed the ping pong table and access to the kayaks. Enjoyed nearby lakes and hiking. Good wifi. Quiet surroundings. Great porch for reading…

$100

The Race Mountain House is set high on the slopes of the Taconic Mountains in Southern Berkshire County. Large, east-facing windows look out over a sweeping view of the Housatonic River Valley. In the early hours, the house floods with warm morning light and sunrises are spectacular. The inviting, creative design …

Perfect weekend getaway!

Left on Feb 12, 2014 for a stay in December 2013

A truly beautiful house in such a magical place! I spent a lovely weekend here with a group of friends from NYC, and we all had our own space to relax, and enjoyed coming together to cook and unwind in the spacious kitchen and living room (the fire place is awesome!). The perfect spot for a peaceful weekend in the woods, plus it's only a short walk to Race Brook Lodge to enjoy some food and …

$175

Two Bedroom two bathroom condo located on beautiful resort in the Berkshires. Oak and Spruce Resort located 15 minutes to Tanglewood is the summer home in the Berkshires of the Boston Symphony Orchestra. Condominium sleeps 6 with an eat in kitchen and living area. Recreational activities, ample parking located in …

$250

Santarella Estate and Gardens in Tyringham, MA is a magical destination in the heart of one of the Berkshires' most beautiful valleys, located 3 miles from Interstate 90 and 15 minutes from most of the principal attractions (Tanglewood, Jacob's Pillow, Norman Rockwell museum, etc.) Pictures are worth a thousand words…

$450

handsome and welcoming, this authentic Berkshire lodge will make you feel like you`re in an old fashioned Christmas card! fireplace blazing, wood floors post and beam, hand planed planks. in the kitchen the floor is marble slabs from the famous lee marble quarry. Daniel Chester French, the designer of the Lincoln …

Beautiful, historic, atmospheric, peaceful, getaway lodge.

Left on Jun 12, 2014 for a stay in August 2013

I had several summer months here, it never disappoints. Full of nature's bounty, hospitable host, friendly vacationers. Very close to all the best of the Berkshires, Tanglewood, dance, theater, Shakespeare, art, homes of historical writers and sculptors. Or just relaxing and reading and often game nights. Smoke free. I look forward to my return.

About Us

Love for FlipKey

As featured in USA TODAY and recommended by Travel + Leisure in its annual Villa Guide:

FlipKey Elsewhere

New to FlipKey?

FlipKey is a vacation rental marketplace with more than 300,000 rentals around the world. Find the perfect place to stay for your trip, and get great value along with the space, privacy and amenities of home.